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#$Date: 2016-03-21 06:43:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178531 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/36/4063664.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4063664
loop_
_publ_author_name
'Fischer, Reinald'
'Langer, Jens'
'Krieck, Sven'
'Görls, Helmar'
'Westerhausen, Matthias'
_publ_section_title
;
 Coordination Behavior of Calcocene and Its Use as a Synthon for
 Heteroleptic Organocalcium Compounds
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1359
_journal_paper_doi               10.1021/om100806f
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C16 H26 Ca N2'
_chemical_formula_sum            'C16 H26 Ca N2'
_chemical_formula_weight         286.47
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.725(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7655(9)
_cell_length_b                   9.1204(5)
_cell_length_c                   13.9518(9)
_cell_measurement_reflns_used    5624
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.85
_cell_volume                     1627.19(18)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5624
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       0.073(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0769
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1335P)²+3.8945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2487
_reflns_number_gt                1489
_reflns_number_total             1841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100806f_si_001.cif
_cod_data_source_block           FO3635
_cod_original_cell_volume        1627.19(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4063664
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ca1 Ca 0.0000 -0.00169(12) 0.2500 0.0412(5) Uani 1 2 d S
N1 N 0.0075(2) -0.2349(5) 0.3630(2) 0.0588(10) Uani 1 1 d .
C1 C 0.1326(3) 0.2102(5) 0.2372(4) 0.0626(12) Uani 1 1 d .
H1A H 0.1022 0.2843 0.1872 0.075 Uiso 1 1 calc R
C2 C 0.1413(3) 0.2134(5) 0.3409(4) 0.0629(12) Uani 1 1 d .
H2A H 0.1187 0.2906 0.3733 0.075 Uiso 1 1 calc R
C3 C 0.1892(3) 0.0833(5) 0.3878(3) 0.0536(10) Uani 1 1 d .
H3A H 0.2041 0.0558 0.4575 0.064 Uiso 1 1 calc R
C4 C 0.2110(3) 0.0006(4) 0.3136(3) 0.0491(9) Uani 1 1 d .
H4A H 0.2440 -0.0927 0.3246 0.059 Uiso 1 1 calc R
C5 C 0.1762(3) 0.0788(5) 0.2205(3) 0.0547(11) Uani 1 1 d .
H5A H 0.1813 0.0481 0.1574 0.066 Uiso 1 1 calc R
C6 C -0.0261(3) -0.3658(5) 0.2897(4) 0.0617(11) Uani 1 1 d .
H6A H -0.1030 -0.3636 0.2533 0.074 Uiso 1 1 calc R
H6B H -0.0079 -0.4577 0.3303 0.074 Uiso 1 1 calc R
C7 C 0.1132(3) -0.2692(6) 0.4354(4) 0.0669(13) Uani 1 1 d .
H7A H 0.1128 -0.3644 0.4678 0.100 Uiso 1 1 calc R
H7B H 0.1363 -0.1931 0.4887 0.100 Uiso 1 1 calc R
H7C H 0.1611 -0.2730 0.3982 0.100 Uiso 1 1 calc R
C8 C -0.0631(3) -0.2324(6) 0.4193(3) 0.0592(11) Uani 1 1 d .
H8A H -0.0530 -0.3215 0.4612 0.089 Uiso 1 1 calc R
H8B H -0.1355 -0.2280 0.3703 0.089 Uiso 1 1 calc R
H8C H -0.0480 -0.1461 0.4644 0.089 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Ca1 N1 71.86(17) 2 .
N1 Ca1 C4 90.60(11) 2 2
N1 Ca1 C4 90.13(11) . 2
N1 Ca1 C4 90.13(11) 2 .
N1 Ca1 C4 90.60(11) . .
C4 Ca1 C4 179.10(17) 2 .
N1 Ca1 C1 114.57(13) 2 .
N1 Ca1 C1 137.69(12) . .
C4 Ca1 C1 129.83(13) 2 .
C4 Ca1 C1 49.33(13) . .
N1 Ca1 C1 137.69(12) 2 2
N1 Ca1 C1 114.57(13) . 2
C4 Ca1 C1 49.33(13) 2 2
C4 Ca1 C1 129.83(13) . 2
C1 Ca1 C1 89.0(2) . 2
N1 Ca1 C5 88.09(12) 2 .
N1 Ca1 C5 118.20(12) . .
C4 Ca1 C5 149.48(13) 2 .
C4 Ca1 C5 30.03(13) . .
C1 Ca1 C5 29.91(14) . .
C1 Ca1 C5 118.68(15) 2 .
N1 Ca1 C5 118.20(12) 2 2
N1 Ca1 C5 88.09(12) . 2
C4 Ca1 C5 30.03(13) 2 2
C4 Ca1 C5 149.48(13) . 2
C1 Ca1 C5 118.68(15) . 2
C1 Ca1 C5 29.91(14) 2 2
C5 Ca1 C5 148.5(2) . 2
N1 Ca1 C3 118.06(11) 2 .
N1 Ca1 C3 89.53(12) . .
C4 Ca1 C3 149.56(13) 2 .
C4 Ca1 C3 29.93(13) . .
C1 Ca1 C3 49.47(15) . .
C1 Ca1 C3 104.05(14) 2 .
C5 Ca1 C3 49.61(13) . .
C5 Ca1 C3 119.56(13) 2 .
N1 Ca1 C3 89.53(12) 2 2
N1 Ca1 C3 118.06(11) . 2
C4 Ca1 C3 29.93(13) 2 2
C4 Ca1 C3 149.56(13) . 2
C1 Ca1 C3 104.05(14) . 2
C1 Ca1 C3 49.47(15) 2 2
C5 Ca1 C3 119.56(13) . 2
C5 Ca1 C3 49.61(13) 2 2
C3 Ca1 C3 146.8(2) . 2
N1 Ca1 C2 136.50(11) 2 .
N1 Ca1 C2 116.19(14) . .
C4 Ca1 C2 129.99(13) 2 .
C4 Ca1 C2 49.17(12) . .
C1 Ca1 C2 30.02(16) . .
C1 Ca1 C2 80.68(13) 2 .
C5 Ca1 C2 49.42(13) . .
C5 Ca1 C2 105.05(13) 2 .
C3 Ca1 C2 29.77(15) . .
C3 Ca1 C2 117.19(15) 2 .
N1 Ca1 C2 116.19(14) 2 2
N1 Ca1 C2 136.50(11) . 2
C4 Ca1 C2 49.17(12) 2 2
C4 Ca1 C2 129.99(13) . 2
C1 Ca1 C2 80.68(13) . 2
C1 Ca1 C2 30.02(16) 2 2
C5 Ca1 C2 105.05(13) . 2
C5 Ca1 C2 49.42(13) 2 2
C3 Ca1 C2 117.19(15) . 2
C3 Ca1 C2 29.77(15) 2 2
C2 Ca1 C2 87.8(2) . 2
C8 N1 C7 108.7(3) . .
C8 N1 C6 106.0(3) . .
C7 N1 C6 105.8(4) . .
C8 N1 Ca1 115.1(3) . .
C7 N1 Ca1 113.3(3) . .
C6 N1 Ca1 107.2(2) . .
C5 C1 C2 108.1(4) . .
C5 C1 Ca1 75.0(2) . .
C2 C1 Ca1 75.5(2) . .
C5 C1 H1A 125.9 . .
C2 C1 H1A 125.9 . .
Ca1 C1 H1A 115.7 . .
C3 C2 C1 108.1(4) . .
C3 C2 Ca1 74.8(2) . .
C1 C2 Ca1 74.4(2) . .
C3 C2 H2A 126.0 . .
C1 C2 H2A 126.0 . .
Ca1 C2 H2A 116.9 . .
C2 C3 C4 107.7(4) . .
C2 C3 Ca1 75.4(2) . .
C4 C3 Ca1 74.7(2) . .
C2 C3 H3A 126.2 . .
C4 C3 H3A 126.2 . .
Ca1 C3 H3A 115.9 . .
C3 C4 C5 108.5(4) . .
C3 C4 Ca1 75.4(2) . .
C5 C4 Ca1 75.1(2) . .
C3 C4 H4A 125.7 . .
C5 C4 H4A 125.7 . .
Ca1 C4 H4A 115.9 . .
C1 C5 C4 107.6(4) . .
C1 C5 Ca1 75.1(2) . .
C4 C5 Ca1 74.9(2) . .
C1 C5 H5A 126.2 . .
C4 C5 H5A 126.2 . .
Ca1 C5 H5A 116.0 . .
N1 C6 C6 112.2(3) . 2
N1 C6 H6A 109.2 . .
C6 C6 H6A 109.2 2 .
N1 C6 H6B 109.2 . .
C6 C6 H6B 109.2 2 .
H6A C6 H6B 107.9 . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 N1 2.627(4) 2
Ca1 N1 2.627(4) .
Ca1 C4 2.705(3) 2
Ca1 C4 2.705(3) .
Ca1 C1 2.709(4) .
Ca1 C1 2.709(4) 2
Ca1 C5 2.707(3) .
Ca1 C5 2.707(3) 2
Ca1 C3 2.715(4) .
Ca1 C3 2.715(3) 2
Ca1 C2 2.723(4) .
Ca1 C2 2.723(4) 2
N1 C8 1.458(5) .
N1 C7 1.465(5) .
N1 C6 1.528(6) .
C1 C5 1.398(7) .
C1 C2 1.407(7) .
C1 H1A 0.9500 .
C2 C3 1.397(7) .
C2 H2A 0.9500 .
C3 C4 1.400(6) .
C3 H3A 0.9500 .
C4 C5 1.402(6) .
C4 H4A 0.9500 .
C5 H5A 0.9500 .
C6 C6 1.527(9) 2
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
